1581771-57-4Relevant academic research and scientific papers
Electrochemical Borylation of Alkyl Halides: Fast, Scalable Access to Alkyl Boronic Esters
Cao, Yangmin,Hu, Ping,Huang, Cheng,Liu, Zhao,Lu, Qingquan,Ma, Wan,Peng, Pan,Qi, Xiaotian,Wang, Bingbing
, p. 12985 - 12991 (2021)
Herein, a fast, scalable, and transition-metal-free borylation of alkyl halides (X = I, Br, Cl) enabled by electroreduction is reported. This process provides an efficient and practical access to primary, secondary, and tertiary boronic esters at a high current. More than 70 examples, including the late-stage borylation of natural products and drug derivatives, are furnished at room temperature, thereby demonstrating the broad utility and functional-group tolerance of this protocol. Mechanistic studies disclosed that B2cat2 serves as both a reagent and a cathodic mediator, enabling electroreduction of difficult-to-reduce alkyl bromides or chlorides at a low potential.
Highly efficient synthesis of alkylboronate esters via Cu(II)-Catalyzed borylation of unactivated alkyl bromides and chlorides in air
Bose, Shubhankar Kumar,Brand, Simon,Omoregie, Helen Oluwatola,Haehnel, Martin,Maier, Jonathan,Bringmann, Gerhard,Marder, Todd B.
, p. 8332 - 8335 (2018/05/22)
A copper(II)-catalyzed borylation of alkyl halides with bis(pinacolato)diboron (B2pin2) has been developed, which can be carried out in air, providing a wide range of primary, secondary, and some tertiary alkylboronates in high yields. A variety of functional groups are tolerated and the protocol is also applicable to unactivated alkyl chlorides (including 1,1- and 1,2-dichlor-ides). Preliminary mechanistic investigations show that this borylation reaction involves one-electron processes.
Zinc-catalyzed borylation of primary, secondary and tertiary alkyl halides with alkoxy diboron reagents at room temperature
Bose, Shubhankar Kumar,Fucke, Katharina,Liu, Lei,Steel, Patrick G.,Marder, Todd B.
supporting information, p. 1799 - 1803 (2014/03/21)
A new catalytic system based on a ZnII NHC precursor has been developed for the cross-coupling reaction of alkyl halides with diboron reagents, which represents a novel use of a Group XII catalyst for C=X borylation. This approach gives borylations of unactivated primary, secondary, and tertiary alkyl halides at room temperature to furnish alkyl boronates, with good functional-group compatibility, under mild conditions. Preliminary mechanistic investigations demonstrated that this borylation reaction seems to involve one-electron processes. Coupling a la carte: A catalytic system based on a ZnII N-heterocyclic carbene precursor has been developed for the cross-coupling reaction of alkyl halides with diboron reagents (see scheme). This is a novel use of a Group 12 catalyst for C=X borylation. IMes=1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene. Copyright
